# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_SKB_OL_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2429151'
loop_
_audit_author_name
_audit_author_address
'Surjya Kumar Bora'
;IIT Guwahati
India
;
_audit_update_record             
;
2025-03-05 deposited with the CCDC.	2025-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 Br N O2 S'
_chemical_formula_sum            'C18 H18 Br N O2 S'
_chemical_formula_weight         392.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.378(2)
_cell_length_b                   8.0513(15)
_cell_length_c                   19.674(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.635(5)
_cell_angle_gamma                90
_cell_volume                     1726.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9562
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      22.32

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   0.3992
_exptl_transmission_factor_max   0.7456
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    2.510
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39994
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.868
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3955
_reflns_number_gt                2546
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0529P)²+1.7176P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3955
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1183
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.04240(4) 0.17139(7) 0.71402(3) 0.0872(2) Uani 1 1 d . . . . .
S1 S 0.35649(9) 0.68646(11) 0.65350(5) 0.0544(2) Uani 1 1 d . . . . .
O1 O 0.4740(2) 0.6372(3) 0.64869(15) 0.0684(7) Uani 1 1 d . . . . .
O2 O 0.3045(3) 0.8423(3) 0.62449(15) 0.0733(8) Uani 1 1 d . . . . .
N1 N 0.2611(2) 0.5443(3) 0.61353(16) 0.0553(7) Uani 1 1 d . . . . .
C1 C 0.2533(3) 0.2968(4) 0.5413(2) 0.0542(8) Uani 1 1 d . . . . .
C2 C 0.3103(4) 0.3499(5) 0.4916(2) 0.0710(11) Uani 1 1 d . . . . .
H2 H 0.372818 0.428224 0.504494 0.085 Uiso 1 1 calc R U . . .
C3 C 0.2755(5) 0.2883(6) 0.4232(3) 0.0827(13) Uani 1 1 d . . . . .
H3 H 0.316011 0.323381 0.390858 0.099 Uiso 1 1 calc R U . . .
C4 C 0.1817(5) 0.1756(6) 0.4028(3) 0.0792(13) Uani 1 1 d . . . . .
H4 H 0.157671 0.135062 0.356623 0.095 Uiso 1 1 calc R U . . .
C5 C 0.1242(4) 0.1236(6) 0.4508(2) 0.0777(12) Uani 1 1 d . . . . .
H5 H 0.060073 0.047747 0.437150 0.093 Uiso 1 1 calc R U . . .
C6 C 0.1603(4) 0.1830(5) 0.5200(2) 0.0666(10) Uani 1 1 d . . . . .
H6 H 0.120765 0.144987 0.552317 0.080 Uiso 1 1 calc R U . . .
C7 C 0.2970(3) 0.3674(4) 0.61625(19) 0.0515(8) Uani 1 1 d . . . . .
H7 H 0.386844 0.362919 0.631193 0.062 Uiso 1 1 calc R U . . .
C8 C 0.1284(3) 0.5740(5) 0.5991(2) 0.0694(11) Uani 1 1 d . . . . .
H8A H 0.089927 0.566904 0.548366 0.083 Uiso 1 1 calc R U . . .
H8B H 0.115790 0.685704 0.614092 0.083 Uiso 1 1 calc R U . . .
C9 C 0.0680(3) 0.4546(5) 0.6356(2) 0.0658(10) Uani 1 1 d . . . . .
H9 H -0.012322 0.474654 0.635880 0.079 Uiso 1 1 calc R U . . .
C10 C 0.1245(3) 0.3211(5) 0.6675(2) 0.0591(9) Uani 1 1 d . . . . .
C11 C 0.2522(3) 0.2727(4) 0.67142(19) 0.0556(9) Uani 1 1 d . . . . .
H11A H 0.255503 0.154234 0.663126 0.067 Uiso 1 1 calc R U . . .
H11B H 0.305584 0.296423 0.718476 0.067 Uiso 1 1 calc R U . . .
C12 C 0.3621(3) 0.6873(4) 0.74358(18) 0.0489(8) Uani 1 1 d . . . . .
C13 C 0.4414(3) 0.5831(4) 0.79107(18) 0.0541(9) Uani 1 1 d . . . . .
H13 H 0.493328 0.512924 0.775498 0.065 Uiso 1 1 calc R U . . .
C14 C 0.4438(4) 0.5829(5) 0.86134(19) 0.0610(9) Uani 1 1 d . . . . .
H14 H 0.498126 0.512995 0.892915 0.073 Uiso 1 1 calc R U . . .
C15 C 0.3671(4) 0.6841(5) 0.8860(2) 0.0595(9) Uani 1 1 d . . . . .
C16 C 0.2890(4) 0.7882(5) 0.8379(2) 0.0693(11) Uani 1 1 d . . . . .
H16 H 0.237410 0.858562 0.853598 0.083 Uiso 1 1 calc R U . . .
C17 C 0.2853(4) 0.7909(5) 0.7672(2) 0.0648(10) Uani 1 1 d . . . . .
H17 H 0.231599 0.861774 0.735778 0.078 Uiso 1 1 calc R U . . .
C18 C 0.3687(5) 0.6819(6) 0.9627(2) 0.0866(14) Uani 1 1 d . . . . .
H18A H 0.371791 0.569129 0.978958 0.130 Uiso 1 1 calc R U . . .
H18B H 0.295784 0.734385 0.967659 0.130 Uiso 1 1 calc R U . . .
H18C H 0.439487 0.740909 0.990558 0.130 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.911(4) . ?
S1 O1 1.424(3) . ?
S1 O2 1.434(3) . ?
S1 N1 1.618(3) . ?
S1 C12 1.755(4) . ?
N1 C8 1.474(5) . ?
N1 C7 1.478(4) . ?
C1 C6 1.372(5) . ?
C1 C2 1.386(6) . ?
C1 C7 1.525(5) . ?
C2 C3 1.381(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.359(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C11 1.529(5) . ?
C7 H7 0.9800 . ?
C8 C9 1.481(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.316(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.485(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.382(5) . ?
C12 C17 1.382(5) . ?
C13 C14 1.375(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.379(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.380(6) . ?
C15 C18 1.505(6) . ?
C16 C17 1.379(6) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 O2 120.36(18) . . ?
O1 S1 N1 106.41(16) . . ?
O2 S1 N1 106.43(16) . . ?
O1 S1 C12 107.73(16) . . ?
O2 S1 C12 106.88(17) . . ?
N1 S1 C12 108.61(16) . . ?
C8 N1 C7 114.9(3) . . ?
C8 N1 S1 119.1(2) . . ?
C7 N1 S1 121.6(2) . . ?
C6 C1 C2 117.8(4) . . ?
C6 C1 C7 123.7(3) . . ?
C2 C1 C7 118.5(3) . . ?
C3 C2 C1 121.0(4) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 121.0(4) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
N1 C7 C1 108.3(3) . . ?
N1 C7 C11 111.2(3) . . ?
C1 C7 C11 114.7(3) . . ?
N1 C7 H7 107.5 . . ?
C1 C7 H7 107.5 . . ?
C11 C7 H7 107.5 . . ?
N1 C8 C9 113.2(3) . . ?
N1 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 122.1(3) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
C9 C10 C11 125.1(4) . . ?
C9 C10 Br1 120.4(3) . . ?
C11 C10 Br1 114.5(3) . . ?
C10 C11 C7 110.7(3) . . ?
C10 C11 H11A 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C17 119.5(3) . . ?
C13 C12 S1 120.6(3) . . ?
C17 C12 S1 119.9(3) . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C14 C15 C16 117.8(4) . . ?
C14 C15 C18 121.2(4) . . ?
C16 C15 C18 121.0(4) . . ?
C17 C16 C15 121.9(4) . . ?
C17 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C16 C17 C12 119.3(4) . . ?
C16 C17 H17 120.3 . . ?
C12 C17 H17 120.3 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C8 -169.8(3) . . . . ?
O2 S1 N1 C8 -40.3(3) . . . . ?
C12 S1 N1 C8 74.5(3) . . . . ?
O1 S1 N1 C7 35.0(3) . . . . ?
O2 S1 N1 C7 164.5(3) . . . . ?
C12 S1 N1 C7 -80.7(3) . . . . ?
C6 C1 C2 C3 -0.9(6) . . . . ?
C7 C1 C2 C3 179.1(4) . . . . ?
C1 C2 C3 C4 1.5(7) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C2 C1 C6 C5 -0.3(6) . . . . ?
C7 C1 C6 C5 179.7(4) . . . . ?
C4 C5 C6 C1 0.9(7) . . . . ?
C8 N1 C7 C1 70.3(4) . . . . ?
S1 N1 C7 C1 -133.5(3) . . . . ?
C8 N1 C7 C11 -56.6(4) . . . . ?
S1 N1 C7 C11 99.6(3) . . . . ?
C6 C1 C7 N1 -110.5(4) . . . . ?
C2 C1 C7 N1 69.4(4) . . . . ?
C6 C1 C7 C11 14.3(5) . . . . ?
C2 C1 C7 C11 -165.7(3) . . . . ?
C7 N1 C8 C9 39.2(5) . . . . ?
S1 N1 C8 C9 -117.6(3) . . . . ?
N1 C8 C9 C10 -10.5(5) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
C8 C9 C10 Br1 179.8(3) . . . . ?
C9 C10 C11 C7 -16.6(5) . . . . ?
Br1 C10 C11 C7 163.5(2) . . . . ?
N1 C7 C11 C10 43.0(4) . . . . ?
C1 C7 C11 C10 -80.3(4) . . . . ?
O1 S1 C12 C13 -28.1(3) . . . . ?
O2 S1 C12 C13 -158.8(3) . . . . ?
N1 S1 C12 C13 86.8(3) . . . . ?
O1 S1 C12 C17 153.0(3) . . . . ?
O2 S1 C12 C17 22.3(3) . . . . ?
N1 S1 C12 C17 -92.1(3) . . . . ?
C17 C12 C13 C14 -0.1(5) . . . . ?
S1 C12 C13 C14 -179.0(3) . . . . ?
C12 C13 C14 C15 0.7(6) . . . . ?
C13 C14 C15 C16 -1.1(6) . . . . ?
C13 C14 C15 C18 179.2(4) . . . . ?
C14 C15 C16 C17 0.9(6) . . . . ?
C18 C15 C16 C17 -179.4(4) . . . . ?
C15 C16 C17 C12 -0.3(6) . . . . ?
C13 C12 C17 C16 -0.1(6) . . . . ?
S1 C12 C17 C16 178.8(3) . . . . ?

_refine_diff_density_max         0.675
_refine_diff_density_min         -0.811
_refine_diff_density_rms         0.069

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_Surjya_0m_a_a
_database_code_depnum_ccdc_archive 'CCDC 2429152'
loop_
_audit_author_name
_audit_author_address
'Surjya Kumar Bora'
;IIT Guwahati
India
;
_audit_update_record             
;
2025-03-05 deposited with the CCDC.	2025-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 Br2 Cl N O2 S'
_chemical_formula_weight         507.66

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4025(12)
_cell_length_b                   15.3012(15)
_cell_length_c                   11.8426(12)
_cell_angle_alpha                90
_cell_angle_beta                 112.487(4)
_cell_angle_gamma                90
_cell_volume                     1909.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6495
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.85

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   0.3144
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    4.507
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18093
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.288
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3358
_reflns_number_gt                2819
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+1.2376P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0011(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3358
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0688
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.10426(3) 0.20024(2) 0.82622(3) 0.04805(14) Uani 1 1 d . . . . .
Br2 Br 0.85931(3) 0.17504(2) 0.59083(3) 0.04846(14) Uani 1 1 d . . . . .
Cl1 Cl 0.68796(12) 0.57497(7) 1.06716(9) 0.0691(3) Uani 1 1 d . . . . .
S1 S 0.74834(7) 0.48952(5) 0.47794(7) 0.02986(18) Uani 1 1 d . . . . .
O1 O 0.69299(19) 0.54374(13) 0.54255(19) 0.0376(5) Uani 1 1 d . . . . .
O2 O 0.8095(2) 0.52863(14) 0.4056(2) 0.0409(5) Uani 1 1 d . . . . .
N1 N 0.8515(2) 0.42724(15) 0.5860(2) 0.0275(5) Uani 1 1 d . . . . .
C1 C 0.6367(3) 0.41760(19) 0.3787(3) 0.0292(6) Uani 1 1 d . . . . .
C2 C 0.5397(3) 0.3937(2) 0.4115(3) 0.0365(7) Uani 1 1 d . . . . .
H2 H 0.530349 0.416704 0.480346 0.044 Uiso 1 1 calc R U . . .
C3 C 0.4561(3) 0.3338(2) 0.3376(3) 0.0422(8) Uani 1 1 d . . . . .
H3 H 0.388839 0.316086 0.358157 0.051 Uiso 1 1 calc R U . . .
C4 C 0.4660(3) 0.2972(2) 0.2315(3) 0.0410(8) Uani 1 1 d . . . . .
C5 C 0.5619(3) 0.3238(2) 0.1985(3) 0.0417(8) Uani 1 1 d . . . . .
H5 H 0.569731 0.302049 0.128405 0.050 Uiso 1 1 calc R U . . .
C6 C 0.6470(3) 0.3834(2) 0.2714(3) 0.0364(7) Uani 1 1 d . . . . .
H6 H 0.713264 0.402098 0.249860 0.044 Uiso 1 1 calc R U . . .
C7 C 0.9192(3) 0.3730(2) 0.5258(3) 0.0342(7) Uani 1 1 d . . . . .
H7A H 0.957778 0.410445 0.483485 0.041 Uiso 1 1 calc R U . . .
H7B H 0.859583 0.334465 0.466277 0.041 Uiso 1 1 calc R U . . .
C8 C 1.0195(3) 0.3203(2) 0.6210(3) 0.0348(7) Uani 1 1 d . . . . .
H8A H 1.083261 0.359750 0.674315 0.042 Uiso 1 1 calc R U . . .
H8B H 1.060687 0.283099 0.580768 0.042 Uiso 1 1 calc R U . . .
C9 C 0.9708(3) 0.26372(19) 0.6981(3) 0.0303(7) Uani 1 1 d . . . . .
C10 C 0.9071(3) 0.31938(18) 0.7622(3) 0.0318(7) Uani 1 1 d . . . . .
H10A H 0.970221 0.355331 0.822869 0.038 Uiso 1 1 calc R U . . .
H10B H 0.868190 0.282072 0.804302 0.038 Uiso 1 1 calc R U . . .
C11 C 0.8056(3) 0.37821(18) 0.6722(3) 0.0280(6) Uani 1 1 d . . . . .
H11 H 0.732656 0.342112 0.623954 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3730(4) 0.2323(3) 0.1521(4) 0.0625(11) Uani 1 1 d . . . . .
H12A H 0.409575 0.202363 0.102149 0.094 Uiso 1 1 calc R U . . .
H12B H 0.297212 0.261996 0.100702 0.094 Uiso 1 1 calc R U . . .
H12C H 0.352427 0.190674 0.202390 0.094 Uiso 1 1 calc R U . . .
C13 C 0.7677(3) 0.43634(18) 0.7584(3) 0.0284(6) Uani 1 1 d . . . . .
C14 C 0.6646(3) 0.4167(2) 0.7823(3) 0.0371(7) Uani 1 1 d . . . . .
H14 H 0.609624 0.373270 0.736940 0.045 Uiso 1 1 calc R U . . .
C15 C 0.6379(3) 0.4602(2) 0.8744(3) 0.0445(8) Uani 1 1 d . . . . .
H15 H 0.565191 0.445276 0.887878 0.053 Uiso 1 1 calc R U . . .
C16 C 0.7154(3) 0.5234(2) 0.9441(3) 0.0419(8) Uani 1 1 d . . . . .
C17 C 0.8173(3) 0.5464(2) 0.9212(3) 0.0429(8) Uani 1 1 d . . . . .
H17 H 0.870387 0.590910 0.965806 0.051 Uiso 1 1 calc R U . . .
C18 C 0.8432(3) 0.5025(2) 0.8288(3) 0.0371(7) Uani 1 1 d . . . . .
H18 H 0.914773 0.518862 0.814455 0.045 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.948(3) . ?
Br2 C9 1.959(3) . ?
Cl1 C16 1.788(3) . ?
S1 O2 1.427(2) . ?
S1 O1 1.429(2) . ?
S1 N1 1.667(2) . ?
S1 C1 1.752(3) . ?
N1 C7 1.487(4) . ?
N1 C11 1.512(3) . ?
C1 C2 1.356(4) . ?
C1 C6 1.420(4) . ?
C2 C3 1.370(4) . ?
C3 C4 1.419(5) . ?
C4 C5 1.356(5) . ?
C4 C12 1.495(4) . ?
C5 C6 1.371(4) . ?
C7 C8 1.499(4) . ?
C8 C9 1.510(4) . ?
C9 C10 1.500(4) . ?
C10 C11 1.530(4) . ?
C11 C13 1.535(4) . ?
C13 C14 1.345(4) . ?
C13 C18 1.383(4) . ?
C14 C15 1.407(4) . ?
C15 C16 1.356(5) . ?
C16 C17 1.336(5) . ?
C17 C18 1.408(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O1 119.71(13) . . ?
O2 S1 N1 109.71(12) . . ?
O1 S1 N1 104.32(12) . . ?
O2 S1 C1 104.92(14) . . ?
O1 S1 C1 111.56(13) . . ?
N1 S1 C1 105.92(13) . . ?
C7 N1 C11 115.1(2) . . ?
C7 N1 S1 107.10(18) . . ?
C11 N1 S1 118.51(17) . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 S1 116.1(2) . . ?
C6 C1 S1 123.0(2) . . ?
C1 C2 C3 116.2(3) . . ?
C2 C3 C4 124.0(3) . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 C12 118.3(3) . . ?
C3 C4 C12 122.8(3) . . ?
C4 C5 C6 118.2(3) . . ?
C5 C6 C1 121.8(3) . . ?
N1 C7 C8 109.1(2) . . ?
C7 C8 C9 114.3(2) . . ?
C10 C9 C8 110.0(2) . . ?
C10 C9 Br1 105.92(19) . . ?
C8 C9 Br1 113.47(19) . . ?
C10 C9 Br2 113.7(2) . . ?
C8 C9 Br2 107.6(2) . . ?
Br1 C9 Br2 106.24(14) . . ?
C9 C10 C11 111.4(2) . . ?
N1 C11 C10 113.4(2) . . ?
N1 C11 C13 114.8(2) . . ?
C10 C11 C13 102.0(2) . . ?
C14 C13 C18 115.4(3) . . ?
C14 C13 C11 120.1(3) . . ?
C18 C13 C11 123.9(3) . . ?
C13 C14 C15 121.6(3) . . ?
C16 C15 C14 121.6(3) . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 Cl1 119.0(3) . . ?
C15 C16 Cl1 122.3(3) . . ?
C16 C17 C18 119.2(3) . . ?
C13 C18 C17 123.5(3) . . ?

_refine_diff_density_max         0.476
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.062

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_skbclbr1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2431627'
loop_
_audit_author_name
_audit_author_address
'Surjya Kumar Bora'
;IIT Guwahati
India
;
_audit_update_record             
;
2025-03-16 deposited with the CCDC.	2025-06-19 downloaded from the CCDC.
;
_audit_creation_date             2025-03-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 Br Cl N O2 S'
_chemical_formula_sum            'C19 H21 Br Cl N O2 S'
_chemical_formula_weight         442.79
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   20.319(4)
_cell_length_b                   10.440(2)
_cell_length_c                   9.3782(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.424(6)
_cell_angle_gamma                90
_cell_volume                     1956.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9958
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      24.42
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.356
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1778 before and 0.1191 after correction.
The Ratio of minimum to maximum transmission is 0.7443.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19480
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.433
_diffrn_reflns_theta_min         2.201
_diffrn_ambient_temperature      295.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           0.0
_diffrn_source_power             0.0
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.980
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                3317
_reflns_number_total             3954
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.150(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3954
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0515
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0958P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1331
_refine_ls_wR_factor_ref         0.1418
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.850(18)
 0.150(18)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
3.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C14(H14), C15(H15), C17(H17), C18(H18)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.49096(6) -0.24247(9) 0.85934(10) 0.0700(3) Uani 1 1 d . . . . .
Cl1 Cl 0.60194(10) -0.3297(2) 0.7085(2) 0.0654(6) Uani 1 1 d . . . . .
S1 S 0.42068(8) -0.22492(17) 0.22839(17) 0.0440(4) Uani 1 1 d . . . . .
O1 O 0.4433(3) -0.1256(6) 0.1406(5) 0.0624(14) Uani 1 1 d . . . . .
O2 O 0.3977(3) -0.3442(6) 0.1637(6) 0.0604(14) Uani 1 1 d . . . . .
N1 N 0.4836(3) -0.2567(5) 0.3575(9) 0.0407(11) Uani 1 1 d . . . . .
C1 C 0.5232(3) -0.1491(6) 0.4318(7) 0.0426(14) Uani 1 1 d . . . . .
H1 H 0.502813 -0.070861 0.385835 0.051 Uiso 1 1 calc R U . . .
C2 C 0.5139(3) -0.1425(7) 0.5925(7) 0.0460(15) Uani 1 1 d . . . . .
H2A H 0.548196 -0.086848 0.645015 0.055 Uiso 1 1 calc R U . . .
H2B H 0.470903 -0.103432 0.595713 0.055 Uiso 1 1 calc R U . . .
C3 C 0.5172(4) -0.2690(7) 0.6697(7) 0.0458(16) Uani 1 1 d . . . . .
C4 C 0.4728(4) -0.3692(7) 0.5846(7) 0.0529(17) Uani 1 1 d . . . . .
H4A H 0.426297 -0.345724 0.579824 0.063 Uiso 1 1 calc R U . . .
H4B H 0.480224 -0.451077 0.633674 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4875(4) -0.3813(7) 0.4318(8) 0.0499(16) Uani 1 1 d . . . . .
H5A H 0.531951 -0.416946 0.436308 0.060 Uiso 1 1 calc R U . . .
H5B H 0.455635 -0.439880 0.376477 0.060 Uiso 1 1 calc R U . . .
C6 C 0.3563(3) -0.1583(7) 0.3090(7) 0.0418(14) Uani 1 1 d . . . . .
C7 C 0.3565(3) -0.0307(7) 0.3393(9) 0.0548(17) Uani 1 1 d . . . . .
H7 H 0.388930 0.022575 0.312648 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3073(4) 0.0198(8) 0.4111(8) 0.0564(17) Uani 1 1 d . . . . .
H8 H 0.308087 0.106409 0.434331 0.068 Uiso 1 1 calc R U . . .
C9 C 0.2578(3) -0.0578(7) 0.4477(6) 0.0484(16) Uani 1 1 d . . . . .
C10 C 0.2587(4) -0.1856(8) 0.4150(8) 0.0535(17) Uani 1 1 d . . . . .
H10 H 0.225742 -0.238788 0.439637 0.064 Uiso 1 1 calc R U . . .
C11 C 0.3073(4) -0.2378(7) 0.3462(10) 0.0506(18) Uani 1 1 d . . . . .
H11 H 0.307064 -0.324915 0.325236 0.061 Uiso 1 1 calc R U . . .
C12 C 0.2048(4) 0.0026(10) 0.5210(9) 0.070(2) Uani 1 1 d . . . . .
H12A H 0.167631 -0.054968 0.515749 0.105 Uiso 1 1 calc R U . . .
H12B H 0.189896 0.081352 0.472875 0.105 Uiso 1 1 calc R U . . .
H12C H 0.223401 0.019740 0.620701 0.105 Uiso 1 1 calc R U . . .
C13 C 0.5951(3) -0.1500(6) 0.4053(6) 0.0417(13) Uani 1 1 d . . . . .
C14 C 0.6130(4) -0.2149(8) 0.2901(9) 0.0543(17) Uani 1 1 d . . . . .
H14 H 0.581380 -0.265446 0.231689 0.065 Uiso 1 1 calc R U . . .
C15 C 0.6768(4) -0.2064(9) 0.2596(10) 0.0613(19) Uani 1 1 d . . . . .
H15 H 0.686750 -0.251105 0.180382 0.074 Uiso 1 1 calc R U . . .
C16 C 0.7260(4) -0.1347(8) 0.3417(8) 0.0567(18) Uani 1 1 d . . . . .
C17 C 0.7075(5) -0.0659(12) 0.4527(10) 0.083(3) Uani 1 1 d . . . . .
H17 H 0.738703 -0.012168 0.507608 0.099 Uiso 1 1 calc R U . . .
C18 C 0.6438(5) -0.0738(11) 0.4858(10) 0.085(3) Uani 1 1 d . . . . .
H18 H 0.633637 -0.027033 0.563433 0.102 Uiso 1 1 calc R U . . .
C19 C 0.7958(4) -0.1270(10) 0.3065(11) 0.074(2) Uani 1 1 d . . . . .
H19A H 0.804873 -0.203404 0.256351 0.111 Uiso 1 1 calc R U . . .
H19B H 0.827909 -0.119039 0.394660 0.111 Uiso 1 1 calc R U . . .
H19C H 0.798840 -0.053860 0.246001 0.111 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.967(6) . ?
Cl1 C3 1.809(7) . ?
S1 O1 1.450(6) . ?
S1 O2 1.426(6) . ?
S1 N1 1.628(8) . ?
S1 C6 1.768(6) . ?
N1 C1 1.480(9) . ?
N1 C5 1.471(9) . ?
C1 H1 0.9800 . ?
C1 C2 1.554(9) . ?
C1 C13 1.526(8) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.501(10) . ?
C3 C4 1.511(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.521(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.362(11) . ?
C6 C11 1.389(11) . ?
C7 H7 0.9300 . ?
C7 C8 1.405(11) . ?
C8 H8 0.9300 . ?
C8 C9 1.383(10) . ?
C9 C10 1.370(11) . ?
C9 C12 1.515(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(11) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.379(10) . ?
C13 C18 1.381(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(11) . ?
C15 H15 0.9300 . ?
C15 C16 1.369(12) . ?
C16 C17 1.371(13) . ?
C16 C19 1.517(11) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(13) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 106.3(3) . . ?
O1 S1 C6 107.3(3) . . ?
O2 S1 O1 119.8(4) . . ?
O2 S1 N1 106.9(3) . . ?
O2 S1 C6 108.3(3) . . ?
N1 S1 C6 107.7(4) . . ?
C1 N1 S1 118.9(4) . . ?
C5 N1 S1 120.0(5) . . ?
C5 N1 C1 118.0(7) . . ?
N1 C1 H1 105.9 . . ?
N1 C1 C2 109.8(6) . . ?
N1 C1 C13 112.0(5) . . ?
C2 C1 H1 105.9 . . ?
C13 C1 H1 105.9 . . ?
C13 C1 C2 116.5(5) . . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 C1 115.2(5) . . ?
C3 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
Cl1 C3 Br1 105.7(3) . . ?
C2 C3 Br1 108.4(5) . . ?
C2 C3 Cl1 111.3(5) . . ?
C2 C3 C4 112.6(6) . . ?
C4 C3 Br1 109.9(5) . . ?
C4 C3 Cl1 108.6(5) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 C5 110.8(6) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
N1 C5 C4 111.6(6) . . ?
N1 C5 H5A 109.3 . . ?
N1 C5 H5B 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 S1 119.9(5) . . ?
C7 C6 C11 120.5(6) . . ?
C11 C6 S1 119.5(5) . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.4(7) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(7) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C12 118.5(7) . . ?
C10 C9 C8 118.4(6) . . ?
C10 C9 C12 123.1(7) . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.8(7) . . ?
C11 C10 H10 119.1 . . ?
C6 C11 H11 120.5 . . ?
C10 C11 C6 119.1(7) . . ?
C10 C11 H11 120.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C1 121.8(6) . . ?
C14 C13 C18 116.6(7) . . ?
C18 C13 C1 121.3(6) . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C15 121.5(7) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 118.8 . . ?
C16 C15 C14 122.4(8) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 C17 116.2(7) . . ?
C15 C16 C19 121.5(8) . . ?
C17 C16 C19 122.3(8) . . ?
C16 C17 H17 118.9 . . ?
C16 C17 C18 122.3(8) . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C17 121.1(8) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C3 C4 C5 174.2(5) . . . . ?
Cl1 C3 C4 C5 -70.6(6) . . . . ?
S1 N1 C1 C2 113.8(7) . . . . ?
S1 N1 C1 C13 -115.2(6) . . . . ?
S1 N1 C5 C4 -107.2(7) . . . . ?
S1 C6 C7 C8 -176.2(5) . . . . ?
S1 C6 C11 C10 177.2(6) . . . . ?
O1 S1 N1 C1 43.2(7) . . . . ?
O1 S1 N1 C5 -157.0(6) . . . . ?
O1 S1 C6 C7 -29.7(7) . . . . ?
O1 S1 C6 C11 152.9(6) . . . . ?
O2 S1 N1 C1 172.3(6) . . . . ?
O2 S1 N1 C5 -28.0(7) . . . . ?
O2 S1 C6 C7 -160.3(6) . . . . ?
O2 S1 C6 C11 22.3(7) . . . . ?
N1 S1 C6 C7 84.4(6) . . . . ?
N1 S1 C6 C11 -93.0(6) . . . . ?
N1 C1 C2 C3 44.1(7) . . . . ?
N1 C1 C13 C14 20.1(9) . . . . ?
N1 C1 C13 C18 -167.5(8) . . . . ?
C1 N1 C5 C4 52.7(9) . . . . ?
C1 C2 C3 Br1 -171.6(5) . . . . ?
C1 C2 C3 Cl1 72.5(6) . . . . ?
C1 C2 C3 C4 -49.7(7) . . . . ?
C1 C13 C14 C15 174.4(7) . . . . ?
C1 C13 C18 C17 -174.0(9) . . . . ?
C2 C1 C13 C14 147.6(7) . . . . ?
C2 C1 C13 C18 -39.9(10) . . . . ?
C2 C3 C4 C5 53.1(8) . . . . ?
C3 C4 C5 N1 -53.5(8) . . . . ?
C5 N1 C1 C2 -46.4(8) . . . . ?
C5 N1 C1 C13 84.7(8) . . . . ?
C6 S1 N1 C1 -71.5(7) . . . . ?
C6 S1 N1 C5 88.3(7) . . . . ?
C6 C7 C8 C9 -1.8(11) . . . . ?
C7 C6 C11 C10 -0.2(12) . . . . ?
C7 C8 C9 C10 1.4(10) . . . . ?
C7 C8 C9 C12 -178.2(7) . . . . ?
C8 C9 C10 C11 -0.4(11) . . . . ?
C9 C10 C11 C6 -0.2(12) . . . . ?
C11 C6 C7 C8 1.2(11) . . . . ?
C12 C9 C10 C11 179.1(7) . . . . ?
C13 C1 C2 C3 -84.5(7) . . . . ?
C13 C14 C15 C16 0.6(14) . . . . ?
C14 C13 C18 C17 -1.2(15) . . . . ?
C14 C15 C16 C17 -3.1(13) . . . . ?
C14 C15 C16 C19 179.8(9) . . . . ?
C15 C16 C17 C18 3.6(15) . . . . ?
C16 C17 C18 C13 -1.5(18) . . . . ?
C18 C13 C14 C15 1.6(13) . . . . ?
C19 C16 C17 C18 -179.4(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.850(18)
2 0.150(18)

